Potassium Hydroxide → HCID 19700418, compound

HRID 861852Notes

Reaction equation

HRID 861852 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[N:12]([C:13](=[O:29])[CH2:14][NH:15][C:16]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([O:27]C)=[O:26])[CH:20]=2)=[O:17])[CH:11]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:10][CH:9]1[S:37]([C:40]1[CH:45]=[CH:44][C:43]([CH3:46])=[CH:42][CH:41]=1)(=[O:39])=[O:38].[OH-].[K+]>CO.O>[C:33]([O:32][C:30]([CH:11]1[CH2:10][CH:9]([S:37]([C:40]2[CH:41]=[CH:42][C:43]([CH3:46])=[CH:44][CH:45]=2)(=[O:38])=[O:39])[CH:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])[N:12]1[C:13](=[O:29])[CH2:14][NH:15][C:16](=[O:17])[NH:18][C:19]1[CH:20]=[C:21]([CH:22]=[CH:23][CH:24]=1)[C:25]([OH:27])=[O:26])=[O:31])([CH3:36])([CH3:34])[CH3:35]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 86752034HCID 86752034, compound

Product 1

HCID 19700418HCID 19700418, compoundYield 12.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A The process is performed as described in Example 1A, but starting with 2.2 g of tert-butyl (2RS,4SR,5RS)-5-(2-fluorophenyl)-1-{2-[3-(3-methoxycarbonylphenyl)ureido]acetyl}-4-(4-methylphenyl)sulphonyl-2-pyrrolidinecarboxylate and 0.19 g of potassium hydroxide in a mixture of 60 cm3 of methanol and 20 cm3 of distilled water. After treatment, 0.27 g of (2RS,4SR,5RS)-3-(3-{2-[2-tert-butoxycarbonyl-5-(2-fluorophenyl)-4-(4-methylphenyl)sulphonyl-1-pyrrolidinyl]-2-oxoethyl}ureido)benzoic acid is obtained [Rf=0.5; eluent: methylene chloride/methanol (90/10); 1H NMR spectrum (200 MHz, (CD3)2SO with addition of a few drops of CD3COOD at a temperature of 373 K, δ in ppm): 1.52 (s, 9H): C(CH3)3); from 2.35 to 2.55 and 2.79 (2 mts, 1H each: CH2 at 3); 2.45 (s, 3H: ArCH3); 3.66 and 3.96 (broad d and d respectively, J=17 Hz, 1H each: COCH2N); 4.05 (mt, 1H: H4); 4.62 (t, J=8 Hz, 1H: H2); 5.70 (d, J=3 Hz, 1H: H5); from 7.00 to 7.55 (mt, 8H: aromatic H); 7.80 (mt, 1H: H of the aromatic at 5 (H6)); 7.85 (d, J=8 Hz, 2H: H of the aromatic at 4 (ortho to the CH3)); 8.00 Ct, J=1.5 Hz, 1H: aromatic H CH2: ortho to the COOH))].

Sources & evidence

ORD record
ord-b8d231271c524f9990895faa1e0cd726
Source dataset
uspto-grants-1998_02
Patent number
US05716936

Reaction notes

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